Thought Leadership

We Need to Talk: The Right Way to Have Critical Conversations at Work

May 18, 2023 | Brown & Brown Insurance | Thought Leadership

We Need to Talk: The Right Way to Have Critical Conversations at Work
by Julie Turpin, Chief People Officer at Brown & Brown Insurance

Does any good leader enjoy having hard conversations with their teams? Most of us don’t. They are called “hard” for a reason.

Yet, does every good leader need to hone their skills at having these types of conversations? Absolutely.

As human beings, we can naturally avoid conflict or awkwardness. We don’t like giving bad news or hurting someone’s feelings. Especially for us women, it’s easy to worry about the Bitch Pitfall, and providing honest feedback or confronting conflict head-on will mark us as “difficult” to work with.

I want to flip the narrative. Instead, let’s think about these difficult conversations — or what I prefer to call honest conversations — as an opportunity to lead with compassion. We show our team members respect and support when we create an open dialogue with them. Directness does not have to be harsh. It can be an act of support.

The difference between a hard conversation and an honest one is in your approach. As always, I recommend leading with vulnerability. Here are three types of conversations you’ll experience as a leader and the mindset I recommend for each:

1) Fostering a graceful exit.

I’ve had to dismiss team members throughout my career, and it’s never an easy task. In these situations, it’s important that we make the other person’s experience a priority and deliver these messages with kindness and compassion. Oftentimes we encourage team members who are leaving to exit with grace, but fostering a graceful exit is also our responsibility as leaders. This includes taking steps before the exit conversation to minimize the shock, such as having regular open dialogues about performance and challenges. When a team member asks me, “How am I performing?” I have to choose to answer with professional honesty, which takes bravery and vulnerability. Shying away from these honest conversations only hurts the other person more in the long term.

2) Confronting tense working relationships.

We’ve all experienced that working situation with a colleague that had us questioning, Do they just not like me? While it can be uncomfortable to confront head-on, it’s often more uncomfortable to try and ignore. It all circles back to vulnerability and finding the courage to ask honest questions like, “Did I do something to upset you?” If your teammate is willing to be equally vulnerable, their answer could open a dialogue that leads to a better working situation.

  • When a working relationship is tense, I like to ask myself:
  • What is my part in this? Have I been unclear or not communicated well?
  • What might this person be going through to cause this exchange?
  • What might their intention in this exchange be?
  • By confronting them, what is my intention? What do I hope to get out of this exchange or relationship?

The key here is to check your intention. If you’re confronting them from a place of anger, you need to reevaluate your approach. In the end, there is something to be learned from each relationship, especially those that challenge you.

3) Giving difficult feedback.

Our primary job as leaders is to give teammates the tools they need to grow. This includes providing honest and direct feedback on performance, especially to our teammates who are struggling. If they understand areas for improvement, they will be better prepared for growth opportunities or future performance discussions. One of the greatest mistakes a leader can make when providing feedback is approaching it from the angle of blame or shame. Instead, we lead with curiosity and conversation. Ask yourself, If someone was giving me this feedback, how would I want to feel? Your answer to this question should lead to how you deliver the message.

The Takeaway: Part of being a leader is guiding peers and teammates through difficult moments. While being distant in these situations could save you from discomfort, support and compassion are often what your team members need. Remember:

  • As leaders, it is our responsibility to initiate regular and open dialogue. Honest conversations around performance and progress should not be solely left to hard times.
  • Being honest and direct does not make one a bitch, especially if shared from a place of compassion and empathy.
  • Honest conversations require vulnerability from both parties.
  • Always consider the other person’s perspective and how you might want to receive the message you are delivering.
  • Make sure your mindset is open, and your intention is pure when you decide to engage someone directly to discuss challenges. The conversation should benefit everyone, not just yourself.


PurposeFULL Leadership
How Personal & Professional Growth Can Help You Lead A Fullfilled Life
by Julie Turpin, Chief People Officer at Brown & Brown Insurance

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